Solar panels and related equipment are frequently mounted on support structures (such as roofs), or other objects that require a substantially water-tight or water resistant connection. For example, solar panels mounted on a tiled roof of a building are commonly attached to the roof via an attachment system that includes a roof hook or flashing device that allows a roof-penetrating member, such as a lag screw, to penetrate a portion of a roofing membrane without compromising the roof's ability to prevent water from entering the building. Prior art attempts to develop such flashing devices have suffered from a number a drawbacks. For example, most flashings are flat and lack the ability to mount solar panels or related equipment on Spanish tile or S tiled roofs. Most conventional flashings are designed for shingled or metal roofs and would require cutting or modifying tiles for installation. Other flashing devices do not provide adequate pressure on the seal around the lag screw. Others do not allow for a separately positionable bracket that enables adjustability relative to the lag screw after installation thereof. Others do not work well with rail-free mounting systems such as those disclosed in prior art patents and other patents and applications of common assignee and at least one common inventor. Others do not comprise a support portion with multiple holes or slots for connecting brackets and/or other devices in various positions to allow for connection to different locations along a photovoltaic (“PV”) module frame. And still others are costly, do not optimize materials usage, create seals from brittle materials that have higher failure rates than resilient materials, require expensive manufacturing methods, and/or do not properly account for misalignment of components during installation. The foregoing examples of the related art and limitations related therewith are intended to be illustrative and not exclusive. Other limitations of the related art will become apparent to those of skill in the art upon a reading of the specification and a study of the figures.